Methanol → Methyl heptanoate

HRID 1733675Notes

Reaction equation

HRID 1733675 reaction equation
[C:1]([OH:9])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:10](N(CC)CC)C.ClC1C=CC(S(ON2C3C=C(Cl)C=CC=3N=N2)(=O)=O)=CC=1.CO>C(Cl)(Cl)Cl>[C:1]([O:9][CH3:10])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 8094Heptanoic AcidHCID 8471Triethylamine2×HCID 122228411-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole

Product 1

HCID 7826Methyl heptanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Heptanoic acid (1.30 g) is dissolved in chloroform (15 ml) and thereto are added triethylamine under ice-cooling and further 1-(p-chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazole (3.44 g), and the mixture is stirred for 3 hours. To the solution are added methanol (0.61 ml) and triethylamine (1.40 ml), whereby exothermic reaction occurs. After stirring for 10 minutes, chloroform is distilled off and to the resulting residue are added water and ether. The ether layer is washed with water, an aqueous sodium hydrogen carbonate and water in order, dried over anhydrous magnesium sulfate and the solvent is distilled off to give methyl heptanoate (1.25 g).

Workup

  1. temperaturecooling
  2. additionTo the solution are added
  3. distillationchloroform is distilled off and to the resulting residue
  4. additionare added water and ether
  5. washThe ether layer is washed with water
  6. dry with materialan aqueous sodium hydrogen carbonate and water in order, dried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-b9745ccc94314acaaefab9b395024cdd
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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